It’s a well-known “secret” that there are wonderful benefits to knowing how to ask the right questions. Professional salespeople often undergo sales training that focuses on determining a prospect’s challenges and needs in order to craft an effective sales pitch. The best way to figure out what those needs are is to ask probing questions. Along a similar vein, successful businesspeople such as Jan Janura have written books (Turning Small Talk Into Big Talk) about developing skills — specifically, the art of questioning — to cultivate more meaningful conversations.

No surprise, then, that the topic is getting ever more attention from the business community. With the rise of Artificial Intelligence (AI), you can generate virtually unlimited answers in an instant. But the key issue is – the answer to what? The answer is only as good as the question asked.

Writing for Harvard Business Review (HBR), Arnaud Chevallier, Frederic Dalsace and Jean-Louis Barsoux note that, “Indeed, leaders have embraced the importance of listening, curiosity, learning, and humility — qualities critical to skillful interrogation. ‘Question-storming’ — brainstorming for questions rather than answers — is now a creativity technique. But unlike lawyers, doctors, and psychologists, business leaders aren’t formally trained on what kinds of questions to ask. They must learn as they go.”

Asking questions, of course, takes time, and time is not unlimited. That means that it’s crucial to ask the right questions. The HBR trio of writers focus on the time problem, saying “If any one line of questioning dominates, it inevitably crowds out others. Leaders must also watch for complacency, diminishing returns, avoidance of sensitive topics, and stubbornness.”

Based on three years of research, the authors go on to group questions into five strategic categories. Before they do that, though, they point out some pitfalls professionals may fall into as they develop their questions. One is simply failing to ask the right questions. “These are questions,” they write, “that don’t come spontaneously; they require prompting and conscious effort. They may run counter to your and your team’s individual or collective habits, preoccupations, and patterns of interaction.”

What might prevent a businessperson from seeking the right line of questioning? Paradoxically, it might be that person’s proven ability to solve problems on their own. “Your professional successes and deep experience,” they write, “may have skewed your approach to problem-solving.”

With all that said, the trio offer five categories of inquiry that are likely to get you on the track to asking the right questions.

• “Investigative: What’s Known.”
• “Speculative: What If?”
• “Productive: Now What?”
• “Interpretive: So, What…?”
• “Subjective: What’s Unsaid?”

Based on these categories, the authors developed a self-assessment and gathered input from 1,200 global executives. Interestingly, each category on average was about evenly represented. However, one or more categories were barely represented in the assessments of over a third of the executives. That means that there is a good possibility that you may not be utilizing one of these categories when you develop the questions you’d like to ask.

The solution is to first determine if you use all five categories. Then get ready to adjust your thinking and style of questioning. If questioning along the lines of one category is difficult for you or makes you uneasy, the authors advise enlisting others and making it a team effort.

Take a deep dive into the HBR article here, which is where you can also find questions taken from the authors’ self-assessment that can help you determine the types of questions you currently favor.